Oldsmar Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Vacation Rentals in Oldsmar

Sailport Waterfront Suites

3.5 star property
8.4 out of 10, Very good, (4623)
"Fantastic stay great area"
The price is CA $151
CA $197 total
includes taxes & fees
Jul 16 - Jul 17
Sailport Waterfront Suites

Sunset Vistas Two Bedroom Beachfront Suites

3.5 star property
8.8 out of 10, Excellent, (3272)
"Beach access and location is excellent "
The price is CA $221
CA $285 total
includes taxes & fees
Jul 27 - Jul 28
Sunset Vistas Two Bedroom Beachfront Suites

The Avalon Club

4.0 star property
9.6 out of 10, Exceptional, (431)
"Beautiful property I would highly recommend this place to anyone looking for clean,friendly,convenience with a beautiful view."
The price is CA $329
CA $419 total
includes taxes & fees
Jul 15 - Jul 16
The Avalon Club

Mint House St. Petersburg - Downtown

4.5 star property
9.4 out of 10, Exceptional, (648)
"Very nice lodging with central location."
The price is CA $136
CA $154 total
includes taxes & fees
Aug 12 - Aug 13
Mint House St. Petersburg - Downtown

John's Pass Hotel

2.0 star property
8.4 out of 10, Very good, (208)
"Efficient and location.was amazing "
The price is CA $169
CA $213 total
includes taxes & fees
Jul 15 - Jul 16
John's Pass Hotel

FUSION Resort Waterfront Suites

3.5 star property
9.2 out of 10, Wonderful, (1041)
"Great place"
The price is CA $256
CA $335 total
includes taxes & fees
Jul 28 - Jul 29
FUSION Resort Waterfront Suites

Westwinds Waterfront Resort

3.0 star property
9.0 out of 10, Wonderful, (672)
"Loved our stay!!! "
The price is CA $168
CA $390 total
includes taxes & fees
Aug 10 - Aug 11
Westwinds Waterfront Resort

Relax on Your Private Beachfront Balcony. Fresh and Comfortable. Great Family Value!

9.4 out of 10, Exceptional, (136)
"Stay was great "
Relax on Your Private Beachfront Balcony. Fresh and Comfortable. Great Family Value!

Beso Del Sol Resort

2.5 star property
8.6 out of 10, Excellent, (630)
"The lady we worked with in the office made the very enjoyable and the surrounding was great "
The price is CA $173
CA $215 total
includes taxes & fees
Jul 15 - Jul 16
Beso Del Sol Resort

Surf Beach Treasure Island Resort

3.0 star property
9.2 out of 10, Wonderful, (807)
"We loved this property. Already planning our next trip there again. The unit was a perfect getaway for our 33rd wedding anniversary. The location is wonderful as well. "
The price is CA $310
CA $598 total
includes taxes & fees
Jul 27 - Jul 28
Surf Beach Treasure Island Resort

South Beach Oceanfront Resort

3.0 star property
9.2 out of 10, Wonderful, (1081)
"We would definitely stay there again…"
The price is CA $199
CA $405 total
includes taxes & fees
Jul 21 - Jul 22
South Beach Oceanfront Resort

Provident Oceana Beachfront Suites

3.5 star property
9.4 out of 10, Exceptional, (573)
"This a great place to stay. Beautiful views, clean, and a short walk to the beach. "
The price is CA $232
CA $290 total
includes taxes & fees
Aug 5 - Aug 6
Provident Oceana Beachfront Suites

The Fold Hotels Indian Shores

3.0 star property
9.2 out of 10, Wonderful, (906)
"Perfect stay! "
The price is CA $200
CA $246 total
includes taxes & fees
Aug 12 - Aug 13
The Fold Hotels Indian Shores

New Beachfront Property in Exclusive Resort

9.6 out of 10, Exceptional, (190)
"Loved the updated room, and proximity to beach!"
The price is CA $197
CA $606 total
includes taxes & fees
Jul 20 - Jul 21
New Beachfront Property in Exclusive Resort

Crystal Palms Beach Resort

3.5 star property
9.0 out of 10, Wonderful, (2330)
"Wry clean and quiet, had a great stay!!$"
The price is CA $170
CA $216 total
includes taxes & fees
Aug 14 - Aug 15
Crystal Palms Beach Resort

The Gemma by Brightwild

5.0 star property
10.0 out of 10, Exceptional, (2)
"Amazing property"
The price is CA $1,411
CA $2,515 total
includes taxes & fees
Jul 15 - Jul 16
The Gemma by Brightwild

WATERFRONT ROOM - The views are incredible!

9.6 out of 10, Exceptional, (9)
"We stayed at this property in celebration of our 25th wedding anniversary and Lauren and the team at The Edge treated us like royalty. Customer service was outstanding… from the friendliness and helpfulness of all staff.. to the Gilberta who left us towel swans and roses on our bed. Thank you all for making our special getaway in Clearwater truly memorable!"
The price is CA $381
CA $616 total
includes taxes & fees
Jul 15 - Jul 16
WATERFRONT ROOM - The views are incredible!

New Tropical Resort Living on the Beach

9.8 out of 10, Exceptional, (161)
"We loved our stay here. The pool and hottub were great and the location was good. "
The price is CA $188
CA $594 total
includes taxes & fees
Jul 20 - Jul 21
New Tropical Resort Living on the Beach

Shoreline Island Resort - Exclusively Adult

3.0 star property
9.2 out of 10, Wonderful, (1352)
"Amazing resort!"
Shoreline Island Resort - Exclusively Adult

Beach Trail Beauty Beachfront Pool Home / Firepit on Gulf

10.0 out of 10, Exceptional, (55)
"The layout of the house was perfect for our adults and children. Would highly recommend this property "
Beach Trail Beauty Beachfront Pool Home / Firepit on Gulf
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Frequently asked questions

Can I find vacation rentals in Oldsmar?

Yes, we have vacation rentals where you'll be just 14.9 mi (23.9 km) from Busch Gardens Tampa Bay, giving you a secluded option to escape the hustle and bustle. Visitors like the top-notch restaurants and beaches in Oldsmar. Make sure you have time to check out the theme park and cafes during your trip.

What are some of the best vacation home rentals in Oldsmar?

The Gemma by Brightwild: You might want to consider this vacation home rental near Oldsmar, which is located on the beach and has an outdoor pool, a private balcony, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a full-sized fridge, a dishwasher, and a stovetop, so you can cook with friends or family. It offers a terrace, a private yard, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals will I find in Oldsmar?

Expedia has 46 vacation rentals for your stay in Oldsmar.

What can I see and do in Oldsmar?

Explore the area and family-friendly sights such as Busch Gardens Tampa Bay, or get out into nature at a spot like Tampa Bay. In the larger area, you’ll find popular places like Raymond James Stadium and Port of Tampa.

What are vacation rentals like in Oldsmar?

Vacation rentals are privately owned properties you can book for a few days or a quick weekend in Oldsmar. Vacation rentals provide amenities such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a vacation rental can offer a sense of security away from public hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for a family trip or a small group gathering.